(+/-)-(5R*)-1-benzyloxy-6-(triisopropylsilyloxy)hex-2-yn-5-ol

Base Information

• Chemical Name: (+/-)-(5R*)-1-benzyloxy-6-(triisopropylsilyloxy)hex-2-yn-5-ol
• CAS No.: 229467-07-6
• Molecular Formula: C₂₂H₃₆O₃Si
• Molecular Weight: 376.612
• Mol file: 229467-07-6.mol

Synonyms:(+/-)-(5R*)-1-benzyloxy-6-(triisopropylsilyloxy)hex-2-yn-5-ol

Chemical Property of (+/-)-(5R*)-1-benzyloxy-6-(triisopropylsilyloxy)hex-2-yn-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-(5R*)-1-benzyloxy-6-(triisopropylsilyloxy)hex-2-yn-5-ol

There total 1 articles about (+/-)-(5R*)-1-benzyloxy-6-(triisopropylsilyloxy)hex-2-yn-5-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 66.0%

Benzyl propargyl ether (4039-82-1) + 2,3-epoxy-1-[(triisopropylsilyl)oxy]propane (152563-54-7) → (+/-)-(5R*)-1-benzyloxy-6-(triisopropylsilyloxy)hex-2-yn-5-ol (229467-07-6)

Guidance literature:

With n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

DOI:10.1016/S0040-4020(99)00149-0

Reference yield: 98.0%

(+/-)-(5R*)-1-benzyloxy-6-(triisopropylsilyloxy)hex-2-yn-5-ol (229467-07-6) → (+/-)-(Z,5R*)-1-benzyloxy-6-(triisopropylsilyloxy)hex-2-en-5-ol (229467-08-7)

Guidance literature:

With hydrogen; Lindlar's catalyst; In ethanol; for 1.66667h;

DOI:10.1016/S0040-4020(99)00149-0

Reference yield:

(+/-)-(5R*)-1-benzyloxy-6-(triisopropylsilyloxy)hex-2-yn-5-ol (229467-07-6) → (+/-)-(2R*,5R*)-2-benzyloxymethyl-5-hydroxymethyl-tetrahydrofuran

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / H₂ / Lindlar / ethanol / 1.67 h

2: 75 percent / VO(acac)2, t-BuOOH / CH₂Cl₂; decane / 1.) 0 deg C, 10 min, 2.) room temperature, 20 h

3: 1.) NaBH₄, 2.) HClO₄ / 1.) EtOH, room temperature, 16 h, 2.) CH₂Cl₂, room temperature, 80 min

4: 80 percent / Bu₃SnH, AIBN / benzene / 1 h / Heating

With tert.-butylhydroperoxide; sodium tetrahydroborate; perchloric acid; bis(acetylacetonate)oxovanadium; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; Lindlar's catalyst; In decane; ethanol; dichloromethane; benzene;

DOI:10.1016/S0040-4020(99)00149-0

upstream raw materials:

Benzyl propargyl ether

2,3-epoxy-1-[(triisopropylsilyl)oxy]propane

Downstream raw materials:

(+/-)-(Z,5R*)-1-benzyloxy-6-(triisopropylsilyloxy)hex-2-en-5-ol